ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 4, Problem 4.34P

Name each alkane using the ball-and-stick model, and classify each carbon as 1 ο , 2 ο , 3 ο , or 4 ο .

Chapter 4, Problem 4.34P, Name each alkane using the ball-and-stick model, and classify each carbon as 1,2,3,or4.

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: The nomenclature of given alkane is to be stated and each carbon as 1ο,2ο,3ο,or4ο is to be classified.

Concept introduction: The aliphatic hydrocarbons that have only CC and CHσ bonds are called alkanes. A primary carbon atom is indicated by 1ο, and it is bonded to only one other carbon atom. A secondary carbon atom is indicated by 2ο, and it is bonded to two other carbon atoms. A tertiary carbon atom is indicated by 3ο, and it is bonded to three other carbon atoms. A quaternary carbon atom is indicated by 4ο, and it is bonded to four other carbon atoms.

Answer to Problem 4.34P

The IUPAC name of given alkane is 3, 3, 4, 5-tetramethylheptane.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.34P , additional homework tip  1

Figure 6

Explanation of Solution

The given ball and stick model of alkane is,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.34P , additional homework tip  2

Figure 1

In ball-and-stick model, each colored ball represents a specific atom and each stick represents a bond. In this model, each black ball represents C atoms,, and each gray ball represents H atoms.

Thus, the skeletal structure of given alkane is,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.34P , additional homework tip  3

Figure 2

One should follow the given four steps to give the IUPAC name of a compound. The first step is naming of longest parent chain.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.34P , additional homework tip  4

Figure 3

The second step is numbering of chain.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.34P , additional homework tip  5

Figure 4

The third step is naming and numbering of substituents.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.34P , additional homework tip  6

Figure 5

The fourth step is combining of all parts.

Substituentsnameandnumbers+Parent+Suffix3, 3, 4, 5-tetramethyl+hept+ane7C’sanalkane

Thus, the IUPAC name of given alkane is 3, 3, 4, 5-tetramethylheptane.

The aliphatic hydrocarbons that have only CC and CHσ bonds are called alkanes. A primary carbon atom is indicated by 1ο, and it is bonded to only one other carbon atom. A secondary carbon atom is indicated by 2ο, and it is bonded to two other carbon atoms. A tertiary carbon atom is indicated by 3ο, and it is bonded to three other carbon atoms. A quaternary carbon atom is indicated by 4ο, and it is bonded to four other carbon atoms.

Thus, each carbon as 1ο,2ο,3ο,or4ο of given alkane is labeled as,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.34P , additional homework tip  7

Figure 6

Conclusion

The IUPAC name of given alkane is 3, 3, 4, 5-tetramethylheptane.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The nomenclature of given alkane is to be stated and each carbon as 1ο,2ο,3ο,or4ο is to be classified.

Concept introduction: The aliphatic hydrocarbons that have only CC and CHσ bonds are called alkanes. A primary carbon atom is indicated by 1ο, and it is bonded to only one other carbon atom. A secondary carbon atom is indicated by 2ο, and it is bonded to two other carbon atoms. A tertiary carbon atom is indicated by 3ο, and it is bonded to three other carbon atoms. A quaternary carbon atom is indicated by 4ο, and it is bonded to four other carbon atoms.

Answer to Problem 4.34P

The IUPAC name of given alkane is 3-ethyl-5, 5-dimethyloctane.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.34P , additional homework tip  8

Figure 12

Explanation of Solution

The given ball and stick model of alkane is,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.34P , additional homework tip  9

Figure 7

In ball-and-stick model, each colored ball represents a specific atom and each stick represents a bond. In this model, each black ball represents C atoms,, and each gray ball represents H atoms.

Thus, the skeletal structure of given alkane is,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.34P , additional homework tip  10

Figure 8

One should follow the given four steps to give the IUPAC name of a compound. The first step is naming of longest parent chain.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.34P , additional homework tip  11

Figure 9

The second step is numbering of chain.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.34P , additional homework tip  12

Figure 10

The third step is naming and numbering of substituents.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.34P , additional homework tip  13

Figure 11

The fourth step is combining of all parts.

Substituentsnameandnumbers+Parent+Suffix3-ethyl-5, 5-dimethyl+oct+ane(Alphabeticalorder:‘e’forethyl,then‘m’formethyl)8C’sanalkane

Thus, the IUPAC name of given alkane is 3-ethyl-5, 5-dimethyloctane.

The aliphatic hydrocarbons that have only CC and CHσ bonds are called alkanes. A primary carbon atom is indicated by 1ο, and it is bonded to only one other carbon atom. A secondary carbon atom is indicated by 2ο, and it is bonded to two other carbon atoms. A tertiary carbon atom is indicated by 3ο, and it is bonded to three other carbon atoms. A quaternary carbon atom is indicated by 4ο, and it is bonded to four other carbon atoms.

Thus, each carbon as 1ο,2ο,3ο,or4ο of given alkane is labeled as,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.34P , additional homework tip  14

Figure 12

Conclusion

The IUPAC name of given alkane is 3, 3, 4, 5-tetramethylheptane.

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Chapter 4 Solutions

ORGANIC CHEMISTRY

Ch. 4 - Give the IUPAC name for each compound.Ch. 4 - Give the structure corresponding to each IUPAC...Ch. 4 - Arrange the following compounds in order of...Ch. 4 - Problem 4.14 Draw the staggered and eclipsed...Ch. 4 - Prob. 4.15PCh. 4 - Prob. 4.16PCh. 4 - Problem 4.17 a. Draw the three staggered and...Ch. 4 - Problem 4.18 Rank the following conformations in...Ch. 4 - Problem 4.19 Consider rotation around the...Ch. 4 - Calculate the destabilization present in each...Ch. 4 - Problem 4.21 Classify the ring carbons as up or...Ch. 4 - Problem 4.22 Using the cyclohexane with the C’s...Ch. 4 - Draw a second chair conformation for each...Ch. 4 - Problem 4.24 Draw both conformations for and...Ch. 4 - Problem 4.25 Draw the structure for each compound...Ch. 4 - For cis-1, 3-diethylcyclobutane, draw a a...Ch. 4 - Prob. 4.27PCh. 4 - Problem 4.28 Consider . Draw structures f or the...Ch. 4 - Problem 4.29 Draw a chair conformation of...Ch. 4 - Prob. 4.30PCh. 4 - Draw the products of each combustion reaction.Ch. 4 - Explain why beeswax is insoluble in H2O, slightly...Ch. 4 - Prob. 4.33PCh. 4 - Name each alkane using the ball-and-stick model,...Ch. 4 - Consider the substituted cyclohexane shown in the...Ch. 4 - Prob. 4.36PCh. 4 - Prob. 4.37PCh. 4 - 4.38 Give the IUPAC name for each compound. a. c....Ch. 4 - 4.39 Give the structure and IUPAC name for each of...Ch. 4 - 4.40 Draw the structure corresponding to each...Ch. 4 - Prob. 4.41PCh. 4 - 4.42 Give the IUPAC name for each compound. a....Ch. 4 - Prob. 4.43PCh. 4 - Prob. 4.44PCh. 4 - 4.45 Which conformation in each pair is higher in...Ch. 4 - 4.46 Considering rotation around the bond...Ch. 4 - Prob. 4.47PCh. 4 - 4.48 (a) Using Newman projections, draw all...Ch. 4 - 4.49 Label the sites of torsional and steric...Ch. 4 - 4.50 Calculate the barrier to rotation for each...Ch. 4 - 4.51 The eclipsed conformation of is less...Ch. 4 - (a) Draw the anti and gauche conformations for...Ch. 4 - For each compound drawn below: a.Label each OH,Br...Ch. 4 - Draw the two possible chair conformations for...Ch. 4 - For each compound drawn below: a. Draw...Ch. 4 - 4.56 Convert each of the following structures into...Ch. 4 - Prob. 4.57PCh. 4 - Prob. 4.58PCh. 4 - 4.59 Classify each pair of compounds as...Ch. 4 - Classify each pair of compounds as constitutional...Ch. 4 - Prob. 4.61PCh. 4 - 4.62 Draw the three constitutional isomers having...Ch. 4 - Prob. 4.63PCh. 4 - 4.64 Draw the products of combustion of each...Ch. 4 - 4.65 Hydrocarbons like benzene are metabolized in...Ch. 4 - Prob. 4.66PCh. 4 - Prob. 4.67PCh. 4 - Cyclopropane and cyclobutane have similar strain...Ch. 4 - Prob. 4.69PCh. 4 - Haloethanes (CH3CH2X,X=Cl,Br,I) have similar...Ch. 4 - Prob. 4.71PCh. 4 - Prob. 4.72PCh. 4 - Consider the tricyclic structure B (a) Label each...Ch. 4 - Read Appendix B on naming branched alkyl...Ch. 4 - Read Appendix B on naming bicyclic compounds. Then...
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